有机化学英文课件chapter11.pptVIP

Organic Chemistry William H. Brown Christopher S. Foote Brent L. Iverson Ethers Epoxides Structure The functional group of an ether is an oxygen atom bonded to two carbon atoms in dialkyl ethers, oxygen is sp3 hybridized with bond angles of approximately 109.5°. in dimethyl ether, the C-O-C bond angle is 110.3° Structure in other ethers, the ether oxygen is bonded to an sp2 hybridized carbon in ethyl vinyl ether, for example, the ether oxygen is bonded to one sp3 hybridized carbon and one sp2 hybridized carbon Nomenclature: ethers IUPAC: the longest carbon chain is the parent name the OR group as an alkoxy substituent Common names: name the groups bonded to oxygen in alphabetical order followed by the word ether Nomenclature: ethers Although cyclic ethers have IUPAC names, their common names are more widely used IUPAC: prefix ox- shows oxygen in the ring the suffixes -irane, -etane, -olane, and -ane show three, four, five, and six atoms in a saturated ring Physical Properties Although ethers are polar compounds, only weak dipole-dipole attractive forces exist between their molecules in the pure liquid state Physical Properties Boiling points of ethers are lower than alcohols of comparable MW close to those of hydrocarbons of comparable MW Ethers are hydrogen bond acceptors they are more soluble in H2O than are hydrocarbons Preparation of Ethers Williamson ether synthesis: SN2 displacement of halide, tosylate, or mesylate by alkoxide ion Preparation of Ethers yields are highest with methyl and 1° halides, lower with 2° halides (competing ?-elimination) reaction fails with 3° halides (?-elimination only) Preparation of Ethers Acid-catalyzed dehydration of alcohols diethyl ether and several other ethers are made on an industrial scale this way a specific example of an SN2 reaction in which a poor leaving group (OH-) is converted to a better one (H2O) Preparation of Ethers Step 1: proton transfer gives an oxonium ion Step 2: nucleophilic displacement of H2O